 At the start of the 2009–10 season, Caicedo was tipped to leave City in order to get more playing time, especially after the club signed fellow forwards Roque Santa Cruz, Emmanuel Adebayor, and Carlos Tevez.On 23 July 2009, Sporting Clube de Portugal and Manchester City reached an agreement over an initial one-year loan with an option of a permanent deal, that would allow him to be part of their squad for the 2009–10 UEFA Champions League, potentially allowing Caicedo a year to develop himself as a forward before returning to Manchester City.Caicedo made his debut for Sporting CP shirt after coming on as a substitute for Hélder Postiga injured on a 36th minutes in a 2–1 loss against Braga on 22 August 2009.